Winter Park

People who live in Winter Park will tell you that Winter Park is not Orlando, that it is its own thing. Though the uninitiated may only notice a change in the color of the street signs, there is a very real attitudinal difference between the two cities. Winter Park is as old as the metropolis to its south, but it has denied itself growth in the service of charm, and that means there’s no more pleasant city in the metro area. Winter Park is brick streets and live oak trees, twee little bakeries serving obscure Portuguese pastries and carefully curated designer boutiques where well-behaved dogs are not only welcome but expected. Homes range from textbook midcentury Florida ranch to gigantic lakeside mansions — the latter coming in two varieties: century-old brick estates and architecturally significant modern masterpieces. The most sought-after properties are on a chain of lakes linked by canals, or within walking distance of Park Avenue, the brick-and-boutique-lined heart of downtown.